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Search results; Over 1,000 places in Near South Side, Chicago

Hotel room in Near North Side
Hotel Perks - Private Bedroom | Private Bathroom
1 queen bed
Apr 20 – 25
4.48 out of 5 average rating, 3620 reviews
Apartment in The Loop
Sentral Premium 2BR Apt South Loop Chicago
2 queen beds
Apr 21 – 26
4.62 out of 5 average rating, 234 reviews
Superhost
Apartment in Chicago
McCormick 2B/2Ba for up to 6 guests w Opt Parking
3 beds
Apr 21 – 26
New place to stay
Guest favorite
Apartment in Chicago
The Central Sanctuary (2BD/2BA)
Apr 22 – 27
4.88 out of 5 average rating, 40 reviews
Superhost
Apartment in Chinatown
Comfy Chinatown Chicago - Central & Close to Train
2 beds
Apr 20 – 25
4.86 out of 5 average rating, 29 reviews
Guest favorite
Apartment in Chicago
McCormick 2B/2Ba for up to 6 guests w Opt Parking
3 beds
Apr 20 – 25
4.93 out of 5 average rating, 30 reviews
Hotel in River North
Playful spirit and sustainable practices
1 queen bed
Apr 20 – 25
4.5 out of 5 average rating, 161 reviews
Boutique hotel in Gold Coast
Luxury Stay - Claridge House, Queen Room
1 queen bed
Apr 28 – May 3
4.43 out of 5 average rating, 689 reviews
Superhost
Apartment in Chicago
Cozy Condo near Downtown Chicago
May 12 – 17
4.81 out of 5 average rating, 16 reviews
Superhost
Hotel in The Loop
A polished, modern affair on iconic Michigan Ave.
1 double bed
Apr 20 – 25
4.8 out of 5 average rating, 41 reviews
Superhost
Apartment in Chicago
McCormick 2B/2Ba for up to 6 guests w Opt Parking
3 beds
Apr 21 – 26
New place to stay
Superhost
Apartment in Chicago
McCormick 2B/2Ba for up to 6 guests w Opt Parking
3 beds
Apr 28 – May 3
New place to stay
Apartment in Chicago
Sonder South Wabash | Studio w/ Courtyard View
1 queen bed
May 1 – 6
4.64 out of 5 average rating, 404 reviews
Superhost
Apartment in Chicago
McCormick Place Studio/parking/sleeps up to 4
2 beds
Apr 21 – 26
4.75 out of 5 average rating, 59 reviews
Guest favorite
Apartment in Little Italy
Newly Renovated 1BD near West Loop & Little Italy
2 beds
Apr 21 – 26
5.0 out of 5 average rating, 26 reviews
Guest favorite
Apartment in Chicago
Sprawling South Loop 3Br/2Ba with parking
3 beds
Apr 27 – May 2
4.97 out of 5 average rating, 116 reviews
Guest favorite
Apartment in Chicago
Location! Location! Location!
1 bed
Jul 3 – 8
4.97 out of 5 average rating, 60 reviews
Superhost
Apartment in Chicago
McCormick Place 3BR/2BA with Optional Parking
3 queen beds
Apr 20 – 25
New place to stay